Chlorocyclohexane → Tricyclohexylbenzene

HRID 1395961Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1(Cl)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C1C=CC=CC=1>[CH:5]1([C:5]2[C:6]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)=[C:7]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[CH:8]=[CH:9][CH:10]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

Conditions

Temperature: 3 °C

Procedure

Aluminum chloride amounting to 6.83 g was added to 20.0 g of benzene and agitated while cooling at 3° C. Then, 40.4 g of cyclohexyl chloride was slowly dropped thereinto. After the completion of the dropping, the mixture was agitated at room temperature for 5 hours and poured into ice water. An organic layer was extracted by use of ethyl acetate, and the obtained organic layer was distilled at 40° C. under reduced pressure and further at 170° C. under reduced pressure. The resultant matter was cooled to room temperature, and 50 ml of acetone was poured thereinto to thereby carry out recrystallization. The crystal obtained by the recrystallization was collected by filtration. Thus, 14 g of tricyclohexylbenzene was obtained.

Workup

stirringAfter the completion of the dropping, the mixture was agitated at room temperature for 5 hours
extractionAn organic layer was extracted by use of ethyl acetate
distillationthe obtained organic layer was distilled at 40° C. under reduced pressure and further at 170° C. under reduced pressure
temperatureThe resultant matter was cooled to room temperature
addition50 ml of acetone was poured
customrecrystallization
customThe crystal obtained by the recrystallization
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-87c240b571e64296b893c4fef78630b5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08900791B2

Reaction notes

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